Ketoreductase-Catalyzed Access to Axially Chiral 2,6-Disubstituted Spiro[3.3]heptane Derivatives

The desymmetrization of a prochiral 6-oxaspiro[3.3]­heptane-2-carboxylic acid derivative via biocatalytic ketoreductase-mediated reduction has provided access to both enantiomers in high ee. The axially chiral alcohol was converted to the corresponding ester alcohol, amino acid, and amino alcohol bu...

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Published inOrganic letters Vol. 24; no. 18; pp. 3431 - 3434
Main Authors O’Dowd, Hardwin, Manske, Jenna L., Freedman, Seth A., Cochran, John E.
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 13.05.2022
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOBUTANES
RESOLUTION
SCAFFOLDS
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Summary:The desymmetrization of a prochiral 6-oxaspiro[3.3]­heptane-2-carboxylic acid derivative via biocatalytic ketoreductase-mediated reduction has provided access to both enantiomers in high ee. The axially chiral alcohol was converted to the corresponding ester alcohol, amino acid, and amino alcohol building blocks while high enantiopurity was maintained.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c01378